Cheshire Academy Leader Selected to Toddle’s 100 Innovative Educators
Woelper among 100 independent school educators recognized for advancing innovation in the curriculum, AI, and school leadership Cheshire Academy Head of School Tom Woelper is one of The 100 Independent School Innovators 2026, a select group of school leaders whose work is making learning more meaningful, more equitable, and more future-facing. Recognized by Toddle, a leading AI-powered platform for teaching and learning, Woelper was invited to join those chosen at The Summit, a December gathering for peer exchange […]
Cheshire Academy Announces New Parent Education and College Finance Series
New workshops, Zooms, and school resources give parents the tools they need and strengthen school-home connections Cheshire Academy is excited to announce two new series of workshops on parenting issues and financial literacy, providing parents and families with up-to-date information to make smart, informed decisions for their students. “A strong partnership between home and school is key to […]
Cheshire Academy Marketing Director Featured on FOX61, Yahoo! News
Sarah LeBlond says critical issues discussed at Connecticut marketing event inform Cheshire Academy intern program, support Strategic Plan Cheshire Academy Director of Marketing & Communication Sarah LeBlond shared with FOX61 News in the Sept. 22 “Live at 5” television broadcast the lessons she planned to share at an event for state marketing leaders. Furthermore, she noted the […]
Independent School Magazine Features Cheshire Academy Head Tom Woelper
Woelper discusses his path to Cheshire Academy and what inspires him in the Fall 2026 issue of Independent School Magazine Recently, Cheshire Academy Head of School Tom Woelper appeared on the National Association of Independent Schools (NAIS) podcast Member Voices to trace his career, how the school is addressing the widespread challenges of financial stability and AI in the space, and the enduring need for empathy and […]
Cheshire Academy Convocation: New Students, New Mascot Name, New Year
New traditions, speeches, songs, and a name for the Cheshire Academy Cat mark annual ceremony on Simosa Field Cheshire Academy opened its 2026-27 academic year on Monday, September 7, with a lively Convocation, featuring songs and speeches from students, and the unveiling of the school mascot’s forever name. A large crowd of family, friends, and alumni attended the event under picture-perfect skies. The 233-year-old school, […]
10 New Faculty Join Cheshire Academy for 2026-27
Each brings a wealth of experience and talent to academics and student support services Cheshire Academy welcomed 10 new faculty members for the 2026-27 academic year, including classroom teachers and student-facing professionals in College Counseling, Campus Life, and the Roxbury Center for Learning & Leadership. “Cheshire Academy continues to attract talented and experienced faculty and staff and I’m looking forward to working with each of […]
From Cheshire Academy Postgrad to West Point and Beyond
By Ben Vasta PG’16 Starting at Cheshire Academy, I’m grateful for all the connections I made with instructors, staff, and students in one short year that I still stay in contact with today. At CA, I learned the value of consistency. Consistent effort in all things compounds into many great things. Whether that’s studying or […]
IB Extended Essay: A Teacher-Student Collaboration
As you likely have read elsewhere, we hosted Yanying “Nicole” Hao ’21 on April 2, 2026, as our third Alumni in the Classroom visitor. It was an exciting and productive visit focused on her many interests and talents. I want to share a personal story about her that gives even more evidence of her intellectual […]
Finding the Perfect ‘Right-Fit’ College
At Cheshire Academy, personalized college counseling from year one is key. In June, 111 students graduated from Cheshire Academy. The list of colleges they went off to was almost as long as their procession, including nearly 80 institutions from Ivies to “Big 10s” to international business heavyweights like Hult International Business School and IEU—Madrid. When Cheshire Academy […]
Meet Cheshire Academy’s New Varsity Head Coaches
Brian Looney, Bradley Orban, Chris Russo, Kevin Warnock bring decades of collegiate, professional and club-level experience to Cheshire Academy’s athletics program. CHESHIRE, Conn.— Cheshire Academy has announced the appointment of four new varsity head coaches to lead the Cats for the 2026-27 year: Brian Looney, baseball; Bradley Orban, boys’ tennis; Chris Russo, girls’ soccer; and Kevin […]
